chemoselectivity

• 官能基選択性、化学選択性

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/11/28 02:36:27」(JST)

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Chemical reactions are defined usually in small contexts (only up to a small number of neighbouring atoms), such generalizations are a matter of utility. The preferential outcome of one instance of a generalized reaction over a set of other plausible reactions, is defined as chemoselectivity.

In another definition, chemoselectivity refers to the selective reactivity of one functional group in the presence of others; often this process in convoluted and protecting groups are on the molecular connectivity alone. Such predictions based on connectivity are generally considered plausible, but the physical outcome of the actual reaction is ultimately dependent on a number of factors that are practically impossible to predict to any useful accuracy (solvent, atomic orbitals, etc.).

As such, chemoselectivity can be difficult to predict, but observing selective outcomes in cases where many reactions are plausible, is common. Examples include the selective organic reduction of the greater relative chemoselectivity of sodium borohydride reduction vs. lithium aluminium hydride reduction. In another example, the compound 4-methoxyacetophenone is oxidized by bleach at the ketone group at high pH (forming the carboxylic acid) and oxidized by EAS (to the aryl chloride) at low pH

See also

• Regioselectivity
• Stereoselectivity

References

English Journal

• Photocycloadditions of substituted oxazoles with isoquinoline-1,3,4-trione-chemo-, regio-, diastereoselectivities and transformation of the photocycloadducts.

• Huang CM, Jiang H, Wang RZ, Quah CK, Fun HK, Zhang Y.SourceSchool of Chemistry and Chemical Engineering, State Key Laboratory of Analytical Chemistry for Life Science, Nanjing University, Nanjing, 210093, P. R. China. njuzy@nju.edu.cn.
• Organic & biomolecular chemistry.Org Biomol Chem.2013 Aug 14;11(30):5023-33. doi: 10.1039/c3ob40645h. Epub 2013 Jun 26.
• Photoreactions of isoquinoline-1,3,4-triones and oxazoles with different substituents were found to give different chemo-, regio- and diastereoselectivities. The substituent at the C5 on the oxazole ring showed great influence on the chemoselectivity of the photoreaction as well as on the transforma
• PMID 23801247

• Synthesis of (-)-epi-indolactam v by an intramolecular buchwald-hartwig C-N coupling cyclization reaction.

• Mari M, Bartoccini F, Piersanti G.SourceDepartment of Biomolecular Sciences, University of Urbino "Carlo Bo" , Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
• The Journal of organic chemistry.J Org Chem.2013 Aug 2;78(15):7727-34. doi: 10.1021/jo4013767. Epub 2013 Jul 25.
• The synthetic efforts toward the concise synthesis of (-)-indolactam V from simple and commercially available starting materials using palladium- and copper-catalyzed intramolecular N-arylation strategy for the elaboration of the requisite nine-membered lactam ring as the key step are described. The
• PMID 23845025

• Assessing the Impact of Electronic and Steric Tuning of the Ligand in the Spin State and Catalytic Oxidation Ability of the FeII(Pytacn) Family of Complexes.

• Prat I, Company A, Corona T, Parella T, Ribas X, Costas M.SourceGrup de Química Bioinorgànica i Supramolecular (QBIS), Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona , Campus Montilivi, E17071 Girona, Catalonia, Spain.
• Inorganic chemistry.Inorg Chem.2013 Jul 31. [Epub ahead of print]
• A family of iron complexes with the general formula [FeII(R,R'Pytacn)(X)2]n+ is described, where R,R'Pytacn is the tetradentate ligand 1-[(4-R'-6-R-2-pyridyl)methyl]-4,7-dimethyl-1,4,7-triazacyclononane, R refers to the group at the α-position of the pyridine, R' corresponds to the group at the γ-
• PMID 23901826

Japanese Journal

• Iron-catalyzed Suzuki–Miyaura Coupling Reaction of Unactivated Alkyl Halides with Lithium Alkynylborates

• , ,
• Chemistry Letters 44(4), 486-488, 2015
• … The reaction shows high chemoselectivity and is applicable to a broad scope of substrates bearing electrophilic functional groups. …
• NAID 130005062130

• Iron-Catalyzed Suzuki–Miyaura Coupling Reaction of Unactivated Alkyl Halides with Lithium Alkynylborates

• , ,
• Chemistry Letters advpub(0), 2015
• … The reaction shows high chemoselectivity and is applicable to a broad scope of substrates bearing electrophilic functional groups. …
• NAID 130004868432

• Selective Hydrogenation of Nitroaromatics by Colloidal Iridium Nanoparticles

• , , ,
• Chemistry Letters 42(9), 1023-1025, 2013
• … Poly(N-vinyl-2-pyrrolidone) (PVP)-stabilized iridium nanoparticles (Ir NPs) showed high chemoselectivity for hydrogenation of nitroaromatics having –CHO, >C=O, –CN, and –Cl functional groups to afford the corresponding aniline compounds under atmospheric hydrogen at room temperature in aqueous–organic biphasic medium. …
• NAID 130004427038

Related Links

• Chemoselectivity - wikidoc

Chemical reactions are defined usually in small contexts (only up to a small number of neighbouring atoms), such generalizations are a matter of utility. The preferential outcome of one instance of a generalized reaction over a set of ...

• IUPAC Gold Book - chemoselectivity (chemoselective)

Chemoselectivity is the preferential reaction of a chemical reagent with one of two or more different functional groups. A reagent has a high chemoselectivity if reaction occurs with only a limited number of different functional groups.

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